1398331-98-0|1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanol| Ambeed

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Quality Control of [ 1398331-98-0 ] Purity: 95% SDS Specification

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Product Details of [ 1398331-98-0 ]

CAS No. :	1398331-98-0
Formula :	C₁₆H₂₃BO₃
M.W :	274.16
SMILES Code :	OC1(C2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2)CCC1
MDL No. :	MFCD18734557

Safety of [ 1398331-98-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1398331-98-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1398331-98-0 ]

[ 1398331-98-0 ] Synthesis Path-Downstream 1~15

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[ 1398331-98-0 ]
[ 1227496-31-2 ]
[ 1467059-95-5 ]

Yield	Reaction Conditions	Operation in experiment
51%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In ethanol; water; toluene; at 110℃; for 2.0h;Inert atmosphere; Microwave irradiation;	A mixture of 5-bromo-6-fluoro-1H-indole-3-carbaldehyde (90 mg, 0.37 mmol), <strong>[1398331-98-0]1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclobutanol</strong> (120 mg, 0.44 mmol), 2 N aqueous potassium carbonate (0.75 mL, 1.49 mmol) in toluene (3.0 mL) and EtOH (1.0 mL) was degassed with N2 for 3 minutes, and treated with [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (30.0 mg, 0.041 mmol). The mixture was subjected to microwave irradiation conditions at 110 C. for 2 hours. The reaction mixture was cooled to room temperature, poured into half-saturated aqueous NH4Cl solution (15 mL) and extracted with EtOAc (6*15 mL). The combined organic layer were washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (9-50% EtOAc/petroleum ether) to afford the title compound (58.0 mg, 51% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 10.0 (s, 1H), 8.42 (s, 1H), 8.20 (d, J=8.00 Hz, 1H), 7.66 (d, J=8.40 Hz, 2H), 7.59 (d, J=8.40 Hz, 2H), 7.50 (d, J=10.80 Hz, 1H), 2.48 (m, 2H), 2.41 (m, 2H), 2.02 (m, 1H), 1.76 (m, 1H).

References: [1]Patent: US2013/267493,2013,A1 .Location in patent: Paragraph 0713.

3
[ 1398331-98-0 ]
[ 1569900-12-4 ]
[ 1569899-86-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; lithium hydroxide; In water; at 80℃; for 3.5h;Inert atmosphere;	1,1'-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (116.0 mg, 0.142 mmol) was added to a solution of (3R,3aR,6R,6aR)-6-((6- chloro-5-iodo-lH-benzo[d]imidazol-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (Intermediate 7) (300.0 mg, 0.710 mmol), l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)cyclobutanol (292.0 mg, 1.065 mmol), and lithium hydroxide (51.0 mg, 2.130 mmol) in degassed 15% water in dioxane (6.02 mL). The reaction mixture heated under N2 at 80 C for 3.5 h, then cooled to RT, and added to stirring EtOAc (200 mL) / water (200 mL). The aqueous layer was separated and back-extracted with EtOAc (5 X 150 mL). The organic layers combined, washed with brine (200 mL), dried over Na2S04, filtered, and evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 40 g silica RediSep Rf Gold column and employing a 0-100% EtOAc / hexane gradient afforded the title compound. LC-MS: calculated for C23H23C1N205 442.13 observed m/e: 443.34 (M+H)+ (Rt 0.89 / 2.0 min).

References: [1]Patent: WO2014/31468,2014,A1 .Location in patent: Page/Page column 115; 116.

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[ 1398331-98-0 ]
[ 1569900-13-5 ]
[ 1569900-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; lithium hydroxide; In water; at 80℃; for 4.0h;Inert atmosphere;	1,1-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (154.0 mg, 0.189 mmol) was added to a solution of (3R,3aR,6R,6aR)-6-((4,6- difluoro-5-iodo-lH-benzo[d]imidazol-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (Intermediate 8, 400 mg, 0.943 mmol), l-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)cyclobutanol (388.0 mg, 1.415 mmol), and lithium hydroxide (67.8 mg, 2.830 mmol) in degassed 15% water in dioxane (8.0 mL). The reaction mixture heated under N2 at 80 C for 4 h. Then the reaction mixture cool to RT and stirred with EtOAc (200 mL) / water (200 mL). The aqueous layer was separated and back-extracted with EtOAc (5 X 200 mL). The organic layers combined, washed with brine (200 mL), dried over Na2S04, filtered, and the filtrate evaporated under reduced pressure. Flash chromatography of the resulting residue utilizing a 40 g silica RediSep Rf Gold column and employing a 0-100% EtOAc / hexane gradient afforded the title compound. LC-MS: calculated for C23H22F2N205 444.15 observed m/e: 445.39 (M+H)+ (Rt 0.90 / 2.0 min).

References: [1]Patent: WO2014/31468,2014,A1 .Location in patent: Page/Page column 118; 119.

5
[ 20870-78-4 ]
[ 1398331-98-0 ]
5-(4-(1-hydroxycyclobutyl)phenyl)indolin-2-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 7987 - 7991.
Angew. Chem.,2019,vol. 131,p. 8071 - 8075,5.
[2]Science,2018,vol. 359,p. 429 - 434.

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[ 73183-34-3 ]
[ 1398331-98-0 ]